For me, it was a long talk I had with a random person on Omegle when that was a thing. I was bored one night so I decided to give it a try and I was matched with someone who I had nearly a 2 hour conversation with. We told jokes, told each other about ourselves, and talked like we were lifelong friends. But, we never did tell each other our names. I could’ve talked to this person all night but the interaction turned for the worst near the end. The person was depressed from what I gathered and the depression arose and the conversation fizzled out. I still think about them nearly 6 years later and hope that they are doing good whoever they were.
Maybe not the strangest but here are 2 from my vacation to London last month:
2 women walking past. One of them says:
“I talk a lot of shit, but my fart is bigger than my shit.”
Then in Covent Garden I met a very polite drug dealer:
Excuse me, do you need any weed or coke? No, well then have a very good evening.
Nice guy, big smile.